FMOC-NLE-OH

Chemical Properties

Uses

reaction suitability

Synthesis

947154-63-4

77284-32-3

V-Fmoc allylglycine (100 mg, 0.296 mmol), degassed dichloromethane (6.0 mL), terminal olefins (1.48 mmol, 5 eq.), and HGII catalyst (9.29 mg, 5 mol%) were added to a Schlenk reaction flask equipped with a magnetic stirring bar in a drying oven under nitrogen atmosphere. After sealing the reaction flask, it was removed from the desiccator and connected to a vacuum system. The reaction vial was placed under a stream of nitrogen and the quick assembly stopper was replaced with a sub-seal with a 26-gauge pinhole to ensure a continuous flow of nitrogen across the top of the reaction system. The reaction mixture was stirred overnight at room temperature, followed by evaporation of all dichloromethane. The residue was washed with hexane (2 x 10 mL) and collected by filtration or centrifugation. The resulting residue was redissolved in methanol (10 mL) and transferred to a Fischer-Porter reaction tube. The reaction tube was filled with hydrogen (60 psi), sealed and stirred overnight at room temperature. Upon completion of the reaction, the mixture was concentrated under vacuum and the residual brown solid was purified by column chromatography to give the pure Fmoc amino acid analog. Alternatively, the residual brown solid is dissolved in a small amount of ether, the insoluble material is removed by filtration, and the filtrate is concentrated under vacuum to give an off-white solid.

References